CA3009256C - Forme cristalline d'un inhibiteur de la tyrosine kinase de bruton (btk) et son procede de preparation - Google Patents

Forme cristalline d'un inhibiteur de la tyrosine kinase de bruton (btk) et son procede de preparation Download PDF

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Publication number
CA3009256C
CA3009256C CA3009256A CA3009256A CA3009256C CA 3009256 C CA3009256 C CA 3009256C CA 3009256 A CA3009256 A CA 3009256A CA 3009256 A CA3009256 A CA 3009256A CA 3009256 C CA3009256 C CA 3009256C
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crystal
crystal form
difluorophenoxy
compound
water
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CA3009256A
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CA3009256A1 (fr
Inventor
Guaili Wu
Zhenjun QIU
Xi LU
Yun Lu
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Jiangsu Hengrui Medicine Co Ltd
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Jiangsu Hengrui Medicine Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne une nouvelle forme cristalline d'un inhibiteur de la BTK et son procédé de préparation. En particulier, la présente invention concerne un cristal de type I de (R)-1-(3- (4-amino-3-(4-(2,6-difluorophénoxy) phényl)-7-hydroxy-1H-pyrorolo [2,3-d]pyridaz-1-yl)pyrrolidin-1-yl)butyl-2-alcyne-1-cétone (composé de formule (I)), ainsi que son procédé de préparation. La forme cristalline de type I du composé de formule (I) obtenu selon la présente invention présente une bonne stabilité cristalline et une bonne stabilité chimique, et le solvant de cristal utilisé présente un niveau de toxicité et de résidus faibles, ce qui la rend plus appropriée pour un traitement clinique.
CA3009256A 2016-01-05 2016-12-20 Forme cristalline d'un inhibiteur de la tyrosine kinase de bruton (btk) et son procede de preparation Active CA3009256C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201610006080 2016-01-05
CN201610006080.0 2016-01-05
PCT/CN2016/111051 WO2017118277A1 (fr) 2016-01-05 2016-12-20 Forme cristalline d'un inhibiteur de la tyrosine kinase de bruton (btk) et son procédé de préparation

Publications (2)

Publication Number Publication Date
CA3009256A1 CA3009256A1 (fr) 2017-07-13
CA3009256C true CA3009256C (fr) 2023-08-22

Family

ID=59273271

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3009256A Active CA3009256C (fr) 2016-01-05 2016-12-20 Forme cristalline d'un inhibiteur de la tyrosine kinase de bruton (btk) et son procede de preparation

Country Status (15)

Country Link
US (1) US10626116B2 (fr)
EP (1) EP3372607B1 (fr)
JP (1) JP6913274B2 (fr)
KR (1) KR102688907B1 (fr)
CN (1) CN107406453B (fr)
AU (1) AU2016384921C1 (fr)
BR (1) BR112018012106B1 (fr)
CA (1) CA3009256C (fr)
ES (1) ES2875384T3 (fr)
HK (1) HK1243419B (fr)
MX (1) MX376500B (fr)
PL (1) PL3372607T3 (fr)
RU (1) RU2728827C2 (fr)
TW (1) TWI726030B (fr)
WO (1) WO2017118277A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6671489B2 (ja) 2016-02-12 2020-03-25 ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法
CA3096414A1 (fr) * 2018-04-13 2019-10-17 Jiangsu Hengrui Medicine Co., Ltd. Procede de preparation d'un compose de pyrroloaminopyridazinone et d'intermediaires de celui-ci
BR112021000964A2 (pt) 2018-07-25 2021-04-20 Novartis Ag inibidores do inflamassoma de nlrp3
WO2020043321A1 (fr) 2018-08-31 2020-03-05 Stichting Katholieke Universiteit Combinaisons synergiques de sensibilisateurs d'agent de déplétion en acides aminés (aadas) et d'agents de déplétion en acides aminés (aada), et leurs procédés thérapeutiques d'utilisation
CN111499642A (zh) * 2019-01-31 2020-08-07 江苏恒瑞医药股份有限公司 吡咯并[2,3-d]哒嗪-7-酮类衍生物的可药用盐、晶型及其制备方法
AR119731A1 (es) 2019-05-17 2022-01-05 Novartis Ag Inhibidores del inflamasoma nlrp3
JP7603618B2 (ja) * 2019-05-31 2024-12-20 江蘇恒瑞医薬股▲ふん▼有限公司 固体分散体およびその調製方法
CN110372562B (zh) * 2019-07-09 2021-04-06 上海再启生物技术有限公司 一种btk激酶抑制剂关键中间体的晶型及其制备方法
CN112745255A (zh) * 2019-10-30 2021-05-04 江苏恒瑞医药股份有限公司 一种btk激酶抑制剂的制备方法
JP2023536944A (ja) * 2020-08-10 2023-08-30 江蘇恒瑞医薬股▲ふん▼有限公司 疾患の治療におけるｂｔｋ阻害剤の使用
US11708366B2 (en) 2020-08-14 2023-07-25 Novartis Ag Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereof
US20220143026A1 (en) 2020-11-12 2022-05-12 Tg Therapeutics, Inc. Triple combination to treat b-cell malignancies
WO2022261138A1 (fr) 2021-06-08 2022-12-15 Tg Therapeutics, Inc. Signalisation d'ikaros perturbée en tant que biomarqueur pour l'inhibition de btk
CN114751850B (zh) * 2022-06-06 2023-08-25 上海再启生物技术有限公司 一种btk激酶抑制剂关键中间体的制备方法
CN114989062A (zh) * 2022-07-04 2022-09-02 上海再启生物技术有限公司 一种btk激酶抑制剂中间体的晶型及其制备方法
UY40374A (es) 2022-08-03 2024-02-15 Novartis Ag Inhibidores de inflamasoma nlrp3

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2652167A1 (fr) * 2006-05-31 2007-12-06 Philip Jones Derives de pyrrolo[1,2-a]pyrazin-1(2h)-one et de pyrrolo[1,2-d][1,2,4]triazin-1(2h)-one utilises en tant qu'inhibiteurs de la poly(adp-ribose)polymerase (parp)
CA2874756C (fr) 2007-03-28 2018-05-29 Pharmacyclics, Inc. Inhibiteurs de la tyrosine kinase de bruton
US7741330B1 (en) * 2009-10-12 2010-06-22 Pharmacyclics, Inc. Pyrazolo-pyrimidine inhibitors of Bruton's tyrosine kinase
WO2011060440A2 (fr) 2009-11-16 2011-05-19 The Regents Of The University Of California Inhibiteurs de kinases
EP2548877A1 (fr) * 2011-07-19 2013-01-23 MSD Oss B.V. Dérivés de 4-(pyridine condensée à 5 chaînons)benzamide comme inhibiteurs de BTK
EP2890691B1 (fr) 2012-08-31 2018-04-25 Principia Biopharma Inc. Dérivés de benzimidazole en tant qu'inhibiteurs d'itk
US8957080B2 (en) * 2013-04-09 2015-02-17 Principia Biopharma Inc. Tyrosine kinase inhibitors
EP3166608B1 (fr) * 2014-07-07 2018-12-12 Jiangsu Hengrui Medicine Co., Ltd. Composés aminopyridazinone à utiliser en tant qu'inhibiteurs de protéines kinases
KR102635949B1 (ko) * 2017-05-18 2024-02-14 지앙수 헨그루이 파마슈티컬스 컴퍼니 리미티드 종양 치료용 약물의 제조에 있어서의 ezh2 억제제 및 btk 억제제의 조합물의 용도

Also Published As

Publication number Publication date
RU2018125277A3 (fr) 2020-02-28
KR102688907B1 (ko) 2024-07-29
WO2017118277A1 (fr) 2017-07-13
EP3372607A4 (fr) 2018-10-03
RU2728827C2 (ru) 2020-07-31
AU2016384921A1 (en) 2018-07-26
ES2875384T3 (es) 2021-11-10
US10626116B2 (en) 2020-04-21
MX376500B (es) 2025-03-07
BR112018012106B1 (pt) 2023-12-12
CA3009256A1 (fr) 2017-07-13
HK1243419B (zh) 2019-11-22
TWI726030B (zh) 2021-05-01
EP3372607A1 (fr) 2018-09-12
BR112018012106A2 (pt) 2018-12-04
AU2016384921B2 (en) 2020-10-15
TW201725207A (zh) 2017-07-16
RU2018125277A (ru) 2020-02-07
CN107406453B (zh) 2018-12-28
KR20180099787A (ko) 2018-09-05
JP2019500357A (ja) 2019-01-10
MX2018008131A (es) 2018-09-03
PL3372607T3 (pl) 2021-09-20
CN107406453A (zh) 2017-11-28
EP3372607B1 (fr) 2021-04-28
US20190010161A1 (en) 2019-01-10
AU2016384921C1 (en) 2021-05-20
JP6913274B2 (ja) 2021-08-04

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